Tuesdays with T4A: Jonathan Sposato (12/10/13)

Jonathan is the chairman of Geekwire LLC. He was the CEO of Picnik, an online photo editing service, which was acquired by Google in 2010. Sposato also took part in the creation of Microsoft’s Xbox. After Microsoft, Sposato’s first big hit was Phatbits, a tech startup that created a platform for developing mini-XML apps or ‘Gadgets.’ Phatbits was purchased by Google in 2005 and became Google Gadgets. Sposato is the first person in history to sell two companies to Google. Jonathan lives in Seattle with his wife and son.

Where did you grow up, and what do you remember most about it?

I moved around a lot when i was little, mostly because my single mom had to rely on various family to take care of me. I most remember NYC and Hong Kong the most. The energy and constant collisions with other human beings was what I remember the best about both of those cities.

What was your first job?

For a couple of summers when I was 12 and13 I went to work for my uncle in the Bay Area before there was really a Silicon Valley. He and his wife left IBM and started a printed circuit board assembly plant right before the personal computer revolution happened. I did everything from sweeping the floors, to prepping components, to soldering… My pay was a new Apple II which I taught myself how to program games on. But mostly I learned how my aunt and uncle created a successful small business that grew. Their rapport with their employees and how they created their company’s culture was formative to me as well. Your team culture and way of doing things can often be an extension of your own personality as a founder or CEO.

What is your first political memory?

My entire 5th grade class chasing me down the hall chanting, “Reagan! Reagan! Reagan!” after he had swept the elections, because I was the only kid who argued for Jimmy Carter during our mock election. It was weird on so many levels. I remember feeling extremely convicted in my opinion that “you guys are all so so wrong” and at the same time feeling really alone. Those two feelings sort of fused for me. To this day, if I find myself in a room where everyone AGREES with me, I start to question my own position…

You are the world’s leading expert on selling companies to Google, as the only person to sell two to the search giant. Was it tough to turn over control of something you built? How did you approach the Picnik sale differently with the experience gained from the Phatbits acquisition?

Haha! Yes, it is always really hard to turn over control. The reason why we become entrepreneurs is precisely because you seek to do things differently from big companies, to move and fail fast, and to eschew a lot of process. So both times it was a little challenging in that regard. Fact is, my first experience with the sale of Phatbits was so positive that I did NOT approach the Picnik transaction much differently, and in retrospect that was a bit of a mistake because Google itself had become a very different company. They were much bigger, had organized into many more divisions with different chiefs, and were about to transition the entire company to go after social. Picnik walked into quite a bit of chaos where it became a protein that couldn’t quite find the right enzyme to bind to (or vice versa). Still though, I learned a tremendous amount both times and like some alien in a sci-fi movie, was able to “sample” some new approaches and new thinking that shifted my overall approach to entrepreneurship…

Who are your role models and why?

Jim Green, Autumn Sample, Sam Kaspick… Seriously, anyone who can take the uber-entrepreneur step of founding a great non-profit with a killer mission and operationalize it like you guys have, has my utmost respect. Keep in mind that I do my entrepreneurial ventures and expect a concrete and quantifiable return, you guys are doing it simply. Because. It’s. Really. Important.

I didn’t mean to duck your question, however, and I would say that one of my role models is STILL Jimmy Carter, and I also would add Warren Buffet for business, and then on weekends and vacation, the incomparable Cary Grant.

As you look at your community, city/state/country, how do you view your role/responsibility as a citizen? Within that context, how do you view your role as citizen in relation to our Government and Democracy?

I think as citizens we have a responsibility to engage, refrain from cynicism, and not “give up.” It’s really easy to give up these days but that accomplishes ZERO. What an amazing blessing it is to be able to live in this country. This is still the best country in which to live, do business, raise children and give them every opportunity to succeed. If I am in a sort of visibility situation for others then i’m happy to be a mouthpiece for how good we have it and to enlist all of us to continue working to make things better.

With respect to government and democracy specifically, I think about the “gentleman farmer” in the Jeffersonian sense. As citizens we can, and should, be many things. We shouldn’t just be business people (or any one thing), but also educators, inventors, activists, disruptors, or civic leaders if need be. Having an amazing opportunity to engage directly with civic leaders through T4A.org has been one way that I’ve broadened in that respect. By the way, the fact that Jefferson was wealthy but was a little mistrustful of the moneyed class is also something I believe in.

Just about everyone (regardless of political affiliation) sees a large gap between our politics (Washington, DC as well as state capitals) and the reality on the issues we face as a Country. Why do you think that is? I know it's a tough question, but what do you think can be done to close that gap?

Absolutely the gap is huge. I often remark that “everything that happens in business is just a conversation between two people” and I think it’s similar in politics. Recently I had a really neat exchange with freshman congressman Derek Kilmer just before the height of the bi-partisan budget gridlock, and in addition to the fact that he’s just a great guy you want to have represent us in Congress, he related the importance of the interpersonal exchanges and the face time between our civic leaders as the true means that anything gets done.

What is your favorite journey?

I think you mean metaphorically but I’ll give you a literal and metaphoric answer. Every morning I take the bus from my house in Seattle to my office downtown. And every morning I see it as a micro journey across the diverse segments of my community. I start out on my own street, then go past some houses a lot bigger than mine, then on down to a very industrial part of town where the train yards are, then past some big tech companies, then past the Dept. of Social Health Services, then finally the financial district.

But speaking of journey, how about i give you my favorite Journey song also? Don’t Stop Believing!

If you could be anyone else for a day, who would you be?

Umm… Beyoncé?

What is your proudest moment?

When my toddler son said, “Dad, I want to be just like you.”

Meet me here:

About us

Tech for America (T4A.org) provides a platform for service minded leaders to solve America’s toughest challenges